(a) Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted. Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

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Answer 1

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Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

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2) The Diels-Alder reaction, developed by German chemists Otto Diels and Kurt Alder (who received the Nobel Prize in 1950 for their discovery), has great synthetic importance due to the possibility of forming an unsaturated six-membered cycle without involving intermediates ionic. About the reaction, answer: (a) Indicate the reagents necessary for the synthesis of the following compounds, indicating who is the diene and who is the dienophile.

Draw and discuss the mechanism (with arrows to show electron movements) of the Diels-Alder reaction between anthracene and maleic anhydride. Draw the orientation and phases of the reacting p-orbitals showing how they overlap in a “suprafacial” geometry to form product

The diene lactone shown in part (a) has one electron-donating group (¬OR) and one electron-withdrawing group(C“O). This diene lactone is sufficiently electron-rich to serve as the diene in a Diels–Alder reaction.(a) What product would you expect to form when this diene reacts with methyl acetylenecarboxylate, a strong dienophile?

Answer 2

Question

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

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Answer 3

Question

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

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Answer 4

Question

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

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Answer 5

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Answer 6

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Answer 7

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Answer 8

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Answer 9

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Answer 10

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Answer 11

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Answer 13

Ch. 26 - Prob. 26.1P Ch. 26 - Prob. 26.2P Ch. 26 - Synthesize each product from the given starting...Ch. 26 - Prob. 26.4P Ch. 26 - Prob. 26.5P Ch. 26 - Prob. 26.6P Ch. 26 - Prob. 26.7P Ch. 26 - Problem 26.8 What starting materials are needed to...Ch. 26 - Prob. 26.9P Ch. 26 - Prob. 26.10P

Solution Summary: The author explains the ring-closing metathesis (RCM) by Grubbs catalyst occurs when the starting material is diene.

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